This chapter aims to shows that both Nietzsche and Kant have a concern with self-cultivation and the flourishing of the self. It highlights the Epicurean dimension of the ideas of both thinkers, no doubt much to the surprise of many readers of the history of modern philosophy since the reading goes against the grain of how both Kant and Nietzsche are typically portrayed, with Kant often associated with a Stoic tradition and Nietzsche associated with a virtue ethicist tradition running from Aristotle to Hume. For both Kant and Nietzsche self-cultivation and an ethics of self-care are to be practised in a spirit of cheerfulness and equanimity. Both are promoting philosophical sobriety. Nietzsche wants a modest human comportment in the world, whilst Kant appeals to a self that can exercise itself ethically by drawing on an Epicurean-inspired teaching of cheerfulness.